Welcome to Hawaii! Paradise on earth! RedAwning has the perfect vacation rental for your island adventures. Beach bungalows, resort condos, and sun-kissed ocean-front villas await. Browse your island destination using the blue location links below or filter your preferences using the panel to the side. RedAwning offers easy, instant, hotel-style reservations and a simplified booking process so you can have your vacation plans covered in no time.

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  1. APARTMENT
    Golf Course Views & Private! Lovely Renovated 2 Bed/2 Bath- Elima Lani 207

    Golf Course Views & Private! Lovely Renovated 2 Bed/...

    Waikoloa, HI

     This stunning 2 bedroom, 2 bathroom condo with gorgeous golf course views has everything you need for a relaxing vacation. The unit has been exquisitely remodeled from top to bottom. Beautiful new floors, cabinets and counters along with all brand...

    Pool Hot Tub
    FREE CANCELLATION

    $164 to $213/night

  2. CONDOMINIUM
    Perfect for Your Vacation!- 2 Bed/2 Bath on the Golf Course

    Perfect for Your Vacation!- 2 Bed/2 Bath on the Golf Cou...

    Waikoloa, HI

     This is an adorable, updated 2 bedroom 2 bath condo located in Waikoloa Village with fairway view. Updated furnishings with great accommodation for the travelers to Hawaii!  There's a fully furnished kitchen, two full bathrooms and two great...

    Pool Hot Tub
    FREE CANCELLATION

    $152 to $183/night

  3. CONDOMINIUM
    New! Updated! Modern, Maui Beachfront with Central A/C

    New! Updated! Modern, Maui Beachfront with Central A/C

    Lahaina, HI

    Most frequently asked questions re: payments, cancellations, our home, and the area, can be answered in the property info, guest reviews, and pictures, below. We kindly ask that you read all of these details, as we offer a lot of amenities that...

    Pool Hot Tub
    FREE CANCELLATION

    $561 to $731/night

  4. CONDOMINIUM
    Hale Welo Ko Olina Beach Villa (B806)

    Hale Welo Ko Olina Beach Villa (B806)

    Kapolei, HI

    Book with confidence! This vacation rental is a LEGAL Oahu vacation rental operating in a Resort Zoned District and is not affected by the passage of Bill 89.LIVE CALENDAR: If the calendar shows as available, the property IS available and can be...

    Pool Hot Tub

    $432 to $1,500/night

  5. CONDOMINIUM
    Noelani #110

    Noelani #110

    Lahaina, HI

    Not one, but two oceanfront pools and a Jacuzzi, what more can you ask for? Unit 110 is a ground floor unit with washer and dryer. New kitchen cabinets and counter tops. You'll love to just walking out from your private lanai right into the...

    Pool Hot Tub
    FREE CANCELLATION

    $296 to $437/night

  6. CONDOMINIUM
    The Plantation #1

    The Plantation #1

    Lahaina, HI

    This condo is new to our rental program and we are excited about it. Recently updated: new beds, flooring, paint, lanai furniture, and kitchen appliances! Three bedrooms and three full baths. Located right down the road from all of the excitement...

    FREE CANCELLATION

    $329 to $437/night

  7. CONDOMINIUM
    Hale Pumehana Ko Olina Beach Villa (O1202)

    Hale Pumehana Ko Olina Beach Villa (O1202)

    Kapolei, HI

    Book with confidence! This vacation rental is a LEGAL Oahu vacation rental operating in a Resort Zoned District and is not affected by the passage of Bill 89.L I V E C A L E N D A RIf the calendar shows as available, the Villa is not reserved and...

    Pool Hot Tub

    $745 to $1,668/night

  8. CONDOMINIUM
    Hale Kai 2 Ko Olina Beach Villa (B906)

    Hale Kai 2 Ko Olina Beach Villa (B906)

    Kapolei, HI

    Book with confidence! This vacation rental is a LEGAL Oahu vacation rental operating in a Resort Zoned District and is not affected by the passage of Bill 89.LIVE CALENDAR: If the calendar shows as available, the property IS available and can be...

    Pool Hot Tub

    $408 to $1,500/night

  9. CONDOMINIUM
    Kihei Kai Nani #4-221

    Kihei Kai Nani #4-221

    Kihei, HI

    Kihei Kai Nani is located right across from the world renowned Kamaole Beach #2. This gorgeous beach is famous for its long sandy shoreline, clean clear water for snorkeling, and great body surfing. Whale watch, paddle board, walk the beach and...

    Pool
    FREE CANCELLATION

    $150 to $219/night

  10. COTTAGE
    International Colony Club #18

    International Colony Club #18

    Lahaina, HI

    Amazing 1300 sq ft 2 bedroom 2 bath cottage located on 10 tropical acres and right by one of the two pools on this property. Great place to relax after a fun day on Maui. Enjoy the beautiful sunsets from the private lanai.The owners haven taken...

    Pool
    FREE CANCELLATION

    $296 to $549/night

  11. CONDOMINIUM
    Wailea Ekolu #805

    Wailea Ekolu #805

    Wailea, HI

    Aloha! Wailea Ekolu 805, a 2-bedroom, 2-bathroom, ground floor unit has new living room furnishings, new window coverings, with a newly painted interior.Beginning in January 2019, the new owners have been updating and making improvements to their...

    Pool
    FREE CANCELLATION

    $249 to $481/night

  12. CONDOMINIUM
    Palms at Wailea #1503

    Palms at Wailea #1503

    Wailea, HI

    The fabulous Keawakapu Beach is just a short 10 minute stroll from the Palms at Wailea. This beach is world famous for its great snorkeling and long white sandy shoreline. The Palms at Wailea is a gorgeous property; lush with tropical landscaping....

    Pool Hot Tub
    FREE CANCELLATION

    $418 to $585/night

  13. CONDOMINIUM
    Waiohuli Beach Hale #D-121

    Waiohuli Beach Hale #D-121

    Kihei, HI

    Waiohuli Beach Hale is a small oceanfront complex located in Kihei Maui Hawaii. This property has a great aloha feeling with a relaxed and quiet atmosphere. Each unit is steps from the ocean and is centrally located to great shopping, restaurants,...

    Pool
    FREE CANCELLATION

    $157 to $277/night

  14. CONDOMINIUM
    Maui Kamaole #J-219

    Maui Kamaole #J-219

    Kihei, HI

    Kamaole Beach III is just across the street from the upscale Maui Kamaole. This property features lush tropical landscaping, two gorgeous pool areas with hot tubs and water features. There are gas grills peppered throughout the property and tennis...

    Pool Hot Tub
    FREE CANCELLATION

    $324 to $486/night

  15. CONDOMINIUM
    Kaanapali Royal B303

    Kaanapali Royal B303

    Lahaina, HI

    Come and enjoy the Kaanapali Royal B303 2 bedroom, 2 bath condo!This beautiful and very spacious 2-bedroom condo, located in the famous Kaanapali Beach Resort area is the perfect getaway for your next Maui vacation! Just walking distance to the...

    Pool Hot Tub
    FREE CANCELLATION

    $236 to $601/night

  16. CONDOMINIUM
    Kamaole Sands #8-310

    Kamaole Sands #8-310

    Kihei, HI

    Kamaole Sands is the premiere property in South Kihei. Located across the street from Kamaole Beach III. Whale watch, swim, snorkel, walk miles on the beach and watch the most amazing sunsets imaginable. There are 15 acres of lush tropical...

    Pool Hot Tub
    FREE CANCELLATION

    $157 to $289/night

  17. HOUSE
    Pair of 2BR Hawaiian Cottages

    Pair of 2BR Hawaiian Cottages

    Honolulu, HI

    Ideal for groups who want both togetherness and privacy, this pair of vintage-inspired Hawaiian cottages are a delightful home base within walking distance to many Honolulu highlights, including legendary Waikiki Beach (20-minute walk), the Honolulu...

    FREE CANCELLATION

    $413 to $493/night

  18. HOUSE
    Ainamalu 29 at Waikoloa Beach Resort

    Ainamalu 29 at Waikoloa Beach Resort

    Waikoloa, HI

    Come and enjoy a luxurious laid-back island living in our new home located in the beautiful new neighborhood in Waikoloa Beach Resort – Ainamalu. This gated community Ainamalu "Protected, Peaceful Land" is the newest resort community in the...

    FREE CANCELLATION

    $481 to $896/night

  19. CONDOMINIUM
    Hale Akala Falls Ko Olina Beach Villa (O121)

    Hale Akala Falls Ko Olina Beach Villa (O121)

    Kapolei, HI

    Book with confidence! This vacation rental is a LEGAL Oahu vacation rental operating in a Resort Zoned District and is not affected by the passage of Bill 89.LIVE CALENDARIf the calendar shows as available, the Villa is not reserved and can be...

    Pool Hot Tub

    $845 to $1,668/night

  20. CONDOMINIUM
    Hale Ohana Ko Olina Beach Villa (B801)

    Hale Ohana Ko Olina Beach Villa (B801)

    Kapolei, HI

    Book with confidence! This vacation rental is a LEGAL Oahu vacation rental operating in a Resort Zoned District and is not affected by the passage of Bill 89.LIVE CALENDAR: If the calendar shows as available, the property IS available and can be...

    Pool Hot Tub

    $548 to $1,784/night

  21. CONDOMINIUM
    Maui Banyan #Q-403A

    Maui Banyan #Q-403A

    Kihei, HI

    Maui Banyan Resort is situated on 8 acres of beautifully landscaped grounds located in South Maui across the street from the popular Kamaole Beach Park II. This white sandy beach is perfect for swimming and snorkeling. It is a 5-minute drive to the...

    FREE CANCELLATION

    $128 to $232/night

  22. CONDOMINIUM
    Palms at Wailea #205

    Palms at Wailea #205

    Wailea, HI

    The fabulous Keawakapu Beach is just a short 10 minute stroll from the Palms at Wailea. This beach is world famous for its great snorkeling and long walking beach. The Palms at Wailea is a gorgeous property; lush with tropical landscaping. There is...

    Pool Hot Tub
    FREE CANCELLATION

    $394 to $814/night

  23. CONDOMINIUM
    Kihei Bay Surf #136

    Kihei Bay Surf #136

    Kihei, HI

    The Kihei Bay Surf is located in North Kihei across the street from the Whale Sanctuary and Kalepolepo Beach and an ancient Hawaiian fishpond. Each studio has a fully equipped kitchen and Cable TV. In addition there is a large pool, hot tub, tennis...

    Pool Hot Tub
    FREE CANCELLATION

    $99 to $173/night

  24. CONDOMINIUM
    Hanalei Colony Resort E3

    Hanalei Colony Resort E3

    Hanalei, HI

    Wow, you'll have this fabulous north shore beach all to yourselves!!! All remaining August 2019 dates now discounted! For over a year now, the North Shore past Hanalei has been closed to everyone except local residents. Wildlife, like fish and...

    Pool
    FREE CANCELLATION

    $488 to $581/night

  25. HOUSE
    Junior Suite Oceanfront #1007

    Junior Suite Oceanfront #1007

    Lahaina, HI

    Our Junior Suite on the TENTH Floor is spacious and well-appointed with a King Bed as well as a sofa bed for the occasional guest. You will find seating arrangements for relaxing and dining. There is plenty of space to store your clothing and...

    Pool Hot Tub
    FREE CANCELLATION

    $278 to $341/night

  26. CONDOMINIUM
    1BR w/ Pools, Steps to Kamaole Beach 3

    1BR w/ Pools, Steps to Kamaole Beach 3

    Kihei, HI

    PROPERTY OVERVIEWSituated directly across from famous Kamaole Beach III, this charming 1BR condo affords a peek-a-boo ocean view and the perfect Maui location - walking distance to excellent restaurants and a short drive to more fantastic dining and...

    Pool
    FREE CANCELLATION

    $112 to $401/night

  27. CONDOMINIUM
    Hale Lalea Ko Olina Beach Villa (B310)

    Hale Lalea Ko Olina Beach Villa (B310)

    Kapolei, HI

    Book with confidence! This vacation rental is a LEGAL Oahu vacation rental operating in a Resort Zoned District and is not affected by the passage of Bill 89.LIVE CALENDAR: If the calendar shows as available, the property IS available and can be...

    Pool Hot Tub

    $833 to $2,016/night

  28. CONDOMINIUM
    Kihei Bay Surf #126

    Kihei Bay Surf #126

    Kihei, HI

    Kihei Bay Surf is located in North Kihei across the street from the Whale Sanctuary and Kalepolepo Beach and an ancient Hawaiian fishpond. Each studio has a fully equipped kitchen and cable TV. In addition there is a large pool, hot tub, tennis...

    Pool Hot Tub
    FREE CANCELLATION

    $103 to $173/night

  29. CONDOMINIUM
    Nohonani #105

    Nohonani #105

    Lahaina, HI

    Unit #105 is a two bedroom, two bath unit just steps away from the beach. The master bedroom has a king-size bed; and twin beds in the guest bedroom. Free parking and WiFi are provided as well.If you have ever dreamt of lying in bed and going to...

    Pool
    FREE CANCELLATION

    $274 to $353/night

  30. CONDOMINIUM
    Kihei Garden Estates #D-201

    Kihei Garden Estates #D-201

    Kihei, HI

    Kihei Garden Estates is a lovely property right across the street from Waiohuli Beach. Kihei Garden Estates boasts a family friendly gathering area, seating up to 25 people to your Bar-B-Q feast under the covered pavilion. Enjoy this full outdoor...

    Pool Hot Tub
    FREE CANCELLATION

    $139 to $231/night